2-Decarboxy-2-hydroxymethyl-3,7-inter-m-phenylene-13,14-didehydro-PGF compounds

ABSTRACT

This invention comprises certain analogs of the prostaglandins in which the C-1 carboxylic is replaced by a primary alcohol and the double bond between C-13 and C-14 is replaced by a triple bond. Also provided in this invention, are novel chemical processes useful in the preparation of the above prostaglandin analogs. These prostaglandin analogs exhibit prostaglandin-like activity, and are accordingly useful for the same pharmacological purposes as the prostaglandins. Among these purposes are blood pressure lowering, labor induction at term, reproductive-cycle regulation, gastric antisecretory action, and the like.

The present application is a divisional application of Ser. No. 814,500, filed July 11, 1977, issued as U.S. Pat. No. 4,134,921 on Jan. 16, 1979; which application is a divisional application of Ser. No. 708,752, filed July 26, 1976, issued as U.S. Pat. No. 4,058,564 on Nov. 15, 1977.

The present invention relates to prostaglandin analogs for which the essential material constituting a disclosure therefor is incorporated by reference here from U.S. Pat. No. 4,058,564, issued Nov. 15, 1977. 

I claim:
 1. A prostaglandin analog of the formula ##STR1## wherein D is ##STR2## wherein R₈ is hydrogen or hydroxy; wherein M₁ is ##STR3## wherein R₅ is hydrogen or methyl; wherein L₁ is ##STR4## or a mixture of ##STR5## wherein R₃ and R₄ are hydrogen, methyl, or fluoro, being the same or different, with the proviso that one of R₃ and R₄ is fluoro only when the other is hydrogen or fluoro;wherein g is one, 2, or 3; and wherein m is one to 5, inclusive.
 2. A prostaglandin analog according to claim 1, wherein D is ##STR6##
 3. A prostaglandin analog according to claim 2, wherein M₁ is ##STR7##
 4. 2-Decarboxy-2-hydroxymethyl-15-epi-3,7-inter-m-phenylene-4,5,6-trinor-13,14-didehydro-PGF₁ β, a prostaglandin analog according to claim
 3. 5. A prostaglandin analog according to claim 2, wherein M₁ is ##STR8##
 6. A prostaglandin analog according to claim 5, wherein m is
 3. 7. A prostaglandin analog according to claim 6, wherein g is
 3. 8. 2-Decarboxy-2-hydroxymethyl-2a,2b-dihomo-3,7-inter-m-phenylene-4,5,6-trinor-15-methyl-13,14-didehydro-PGF₁ β, a prostaglandin analog according to claim
 7. 9. 2-Decarboxy-2-hydroxymethyl-2a,2b-dihomo-3,7-inter-m-phenylene-4,5,6-trinor-13,14-didehydro-PGF₁ β, a prostaglandin analog according to claim
 7. 10. A prostaglandin analog according to claim 6, wherein g is
 1. 11. A prostaglandin analog according to claim 10, wherein at least one of R₃ and R₄ is methyl.
 12. A prostaglandin analog according to claim 11, wherein R₃ and R₄ are both methyl.
 13. 2-Decarboxy-2-hydroxymethyl-16,16-dimethyl-3,7-inter-m-phenylene-4,5,6-trinor-13,14-didehydro-PGF₁ β, a prostaglandin analog according to claim
 12. 14. A prostaglandin analog according to claim 10, wherein at least one of R₃ and R₄ is fluoro.
 15. A prostaglandin analog according to claim 14, wherein R₃ and R₄ are both fluoro.
 16. 2-Decarboxy-2-hydroxymethyl-3,7-inter-m-phenylene-4,5,6-trinor-16,16-difluoro-13,14-didehydro-PGF₁ β, a prostaglandin analog according to claim
 1. 17. A prostaglandin analog according to claim 10, wherein R₃ and R₄ are both hydrogen.
 18. A prostaglandin analog according to claim 17, wherein R₅ is methyl.
 19. 2-Decarboxy-2-hydroxymethyl-3,7-inter-m-phenylene-4,5,6-trinor-15-methyl-13,14-didehydro-PGF₁ β, a prostaglandin analog according to claim
 18. 20. A prostaglandin analog according to claim 17, wherein R₅ is hydrogen.
 21. 2-Decarboxy-2-hydroxymethyl-3,7-inter-m-phenylene-4,5,6-trinor-13,14-didehydro-PGF₁ β, a prostaglandin analog according to claim
 20. 22. A prostaglandin analog according to claim 1, wherein D is ##STR9##
 23. A prostaglandin analog according to claim 22, wherein M₁ is ##STR10##
 24. A prostaglandin analog according to claim 23, wherein m is
 3. 25. A prostaglandin analog according to claim 23, wherein g is
 3. 26. 2-Decarboxy-2-hydroxymethyl-2a,2b-dihomo-3,7-inter-m-phenylene-4,5,6-trinor-15-epi-15-methyl-13,14-didehydro-PGF₁ β, a prostaglandin analog according to claim
 25. 27. 2-Decarboxy-2-hydroxymethyl-2a,2b-dihomo-3,7-inter-m-phenylene-4,5,6-trinor-15-epi-13,14-didehydro-PGF₁ β, a prostaglandin analog according to claim
 25. 28. A prostaglandin analog according to claim 24, wherein g is
 1. 29. A prostaglandin analog according to claim 28, wherein at least one of R₃ and R₄ is methyl.
 30. 2-Decarboxy-2-hydroxymethyl-15-epi-3,7-inter-m-phenylene-4,5,6-trinor-16,16-dimethyl-13,14-didehydro-PGF₁ β, a prostaglandin analog according to claim
 29. 31. A prostaglandin analog according to claim 28, wherein at least one of R₃ and R₄ is fluoro.
 32. 2-Decarboxy-2-hydroxymethyl-3,7-inter-m-phenylene-4,5,6-trinor-15-epi-16,16-difluoro-13,14-didehydro-PGF₁ β, a prostaglandin analog according to claim
 31. 33. A prostaglandin analog according to claim 28, wherein R₃ and R₄ are both hydrogen.
 34. 2-Decarboxy-2-hydroxymethyl-3,7-inter-m-phenylene-4,5,6-trinor-15-epi-15-methyl-13,14-didehydro-PGF₁ β, a prostaglandin analog according to claim
 33. 35. A prostaglandin analog according to claim 22, wherein M₁ is ##STR11##
 36. A prostaglandin analog according to claim 35, wherein m is
 3. 37. A prostaglandin analog according to claim 36, wherein g is
 3. 38. A prostaglandin analog according to claim 37, wherein at least one of R₃ and R₄ is methyl.
 39. 2-Decarboxy-2-hydroxymethyl-2a,2b-dihomo-3,7-inter-m-phenylene-4,5,6-trinor-16,16-dimethyl-13,14-didehydro-PGF₁ β, a prostaglandin analog according to claim
 38. 40. A prostaglandin analog according to claim 37, wherein at least one of R₃ and R₄ is fluoro.
 41. 2-Decarboxy-2-hydroxymethyl-2a,2b-dihomo-3,7-inter-m-phenylene-4,5,6-trinor-16,16-difluoro-13,14-didehydro-PGF₁ β, a prostaglandin analog according to claim
 40. 42. A prostaglandin analog according to claim 37, wherein R₃ and R₄ are both hydrogen.
 43. 2-Decarboxy-2-hydroxymethyl-2a,2b-dihomo-3,7-inter-m-phenylene-4,5,6-trinor-15-methyl-13,14-didehydro-PGF₁ β, a prostaglandin analog according to claim
 42. 44. A prostaglandin analog according to claim 36, wherein g is
 1. 45. A prostaglandin analog according to claim 44, wherein at least one of R₃ and R₄ is methyl.
 46. A prostaglandin analog according to claim 45, wherein only one of R₃ and R₄ is methyl.
 47. 2-Decarboxy-2-hydroxymethyl-3,7-inter-m-phenylene-4,5,6-trinor-16-methyl-13,14-didehydro-PGF₂ β, a prostaglandin analog according to claim
 46. 48. A prostaglandin analog according to claim 45, wherein R₃ and R₄ are both methyl.
 49. 2-Decarboxy-2-hydroxymethyl-3,7-inter-m-phenylene-4,5,6-trinor-16,16-dimethyl-13,14-didehydro-PGF₁ β, a prostaglandin analog according to claim
 48. 50. A prostaglandin analog according to claim 44, wherein at least one of R₃ and R₄ is fluoro.
 51. A prostaglandin analog according to claim 50, wherein R₃ and R₄ are both fluoro.
 52. A prostaglandin analog according to claim 51, wherein R₅ is methyl.
 53. 2-Decarboxy-2-hydroxymethyl-3,7-inter-m-phenylene-4,5,6-trinor-15-methyl-16,16-difluoro-13,14-didehydro-PGF₁ β, a prostaglandin analog according to claim
 52. 54. A prostaglandin analog according to claim 51, wherein R₅ is hydrogen.
 55. 2-Decarboxy-2-hydroxymethyl-3,7-inter-m-phenylene-4,5,6-trinor-16,16-difluoro-13,14-didehydro-PGF₁ β, a prostaglandin analog according to claim
 54. 56. A prostaglandin analog according to claim 44, wherein R₃ and R₄ are both hydrogen.
 57. A prostaglandin analog according to claim 56, wherein R₅ is methyl.
 58. 2-Decarboxy-2-hydroxymethyl-3,7-inter-m-phenylene-4,5,6-trinor-15-methyl-13,14-didehydro-PGF₁ β, a prostaglandin analog according to claim
 57. 59. A prostaglandin analog according to claim 56, wherein R₅ is hydrogen.
 60. 2-Decarboxy-2-hydroxymethyl-3,7-inter-m-phenylene-4,5,6-trinor-13,14-dihydro-PGF.sub.1 β, a prostaglandin analog according to claim
 59. 